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Journal of Natural Medicines
Erschienen in:

27.01.2022 | Original Paper

Is 18α-Glycyrrhizin a real natural product? Improved preparation of 18α-Glycyrrhizin from 18β-Glycyrrhizin as a positive standard for HPLC analysis of licorice extracts

verfasst von: Kritamorn Jitrangsri, Kazuaki Kamata, Mana Akiba, Yoshie Yajiri, Masami Ishibashi, Jin Tatsuzaki, Tsutomu Ishikawa

Erschienen in: Journal of Natural Medicines | Ausgabe 2/2022

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Abstract

18α-Glycyrrhizin is an epimer of 18β-glycyrrhizin, a major component of licorice (Glycyrrhiza sp.), which is widely used as a traditional medicine. Whether 18α-glycyrrhizin is a real natural product has been debated in the long history of glycyrrhizin chemistry because 18β-glycyrrhizin is epimerizable to a more thermodynamically stable 18α-glycyrrhizin under aqueous alkali conditions. We improved the preparation of 18α-glycyrrhizin from 18β-glycyrrhizin by successive epimerization reactions of 18β-glycyrrhizin, trimethyl esterification of the resulting epimerized mixture, and alkaline hydrolysis of a purified 18α-glycyrrhizin trimethyl ester. Approaches to the possible presence of 18α-glycyrrhizin in licorice extracts by HPLC using synthetic 18α-glycyrrhizin as a positive standard strongly suggested that 18α-glycyrrhizin could naturally exist as a minor congener of glycyrrhizin derivatives in Glycyrrhiza species.

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Metadaten
Titel
Is 18α-Glycyrrhizin a real natural product? Improved preparation of 18α-Glycyrrhizin from 18β-Glycyrrhizin as a positive standard for HPLC analysis of licorice extracts
verfasst von
Kritamorn Jitrangsri
Kazuaki Kamata
Mana Akiba
Yoshie Yajiri
Masami Ishibashi
Jin Tatsuzaki
Tsutomu Ishikawa
Publikationsdatum
27.01.2022
Verlag
Springer Singapore
Erschienen in
Journal of Natural Medicines / Ausgabe 2/2022
Print ISSN: 1340-3443
Elektronische ISSN: 1861-0293
DOI
https://doi.org/10.1007/s11418-021-01589-9

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